Vacation Rentals & House Rentals in Key West

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139 house rentals

$95/night & up in Paradise! South of 5th Art Deco

Miami Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect location for Gramma and her granddaughter to discover So” Loved the location! Loved the management! Loved the unit! Check in was smooth, parking manageable at 10 dollars a day, the unit was a delightful bright one bedroom full kitchen cute living area just perfect down to the internet connection and Tvand washer and dryer... We had a cozy little spot to come and go from all day long, beach, kids park, great walks, and Ocean drive! Close to Bayside and a smooth drive to Marlins Park. So many restaurants and so little time we had to extend!

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$258

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Miami Beach! Beautifull bay view 15th for 4 guests

North Bay Village apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 27 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$171

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$166

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$516

Luxurious 1BED/1.5B A Suite w/Kitchen& Rooftop Pool

Miami Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$607

Luxury Condo, High Floor, Euro Design

Miami apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$123

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$525

The Netherland R5F - Ocean Dr. Condo by Miami Beach Ocean Rental

Miami Beach apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

“Great location in SB!!!!!” This condo is a great little Gem - right on Ocean Drive in SB. Pretty & not to mention spacious kitchen, good living area and the rooms are very clean and big to be at the beach. Near everything: shops, food and best thing is it is right on the strip to the beach. In town for company trip 3 guys very spacious and perfect location to all the hip spots. Giulio (owner) is "Great"!!! he is quick to respond to emails will answer all questions and the best thing is he gets right back to you. I am booking my next trip with Giulio to stay at the Netherlands to have some Miami fun in the sun :)

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$374

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$525

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$488

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$803

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$745

WOW! Best Ocean Front Suite on South Beach

Miami Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$859

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$431

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$123

Responds fast! avg. 2 hours 42 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$142

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$264

Beautiful Villa with heated pool, Fits 14 !

Miami Shores villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,778

Four Seasons 2 bedroom suite

Miami apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$981

Brand new Villa with Pool / Jacuzzi / GameRoom

Coral Gables villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$1,663

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$343

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$307

Stunning Views, Gorgeous 2 bed/2 bath, South Beach

Miami Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$364

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$655

Fontainebleau Hotel Junior Suite, No Resort Fee

Miami Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 30 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$240

Oceanview Penthouse on Ocean Drive w/ private rooftop and Hot Tub

Miami Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 30 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$228

Responds fast! avg. 2 hours 30 minutes

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$228

DreamVilla / Pool! Brand New Modern Construction!

Miami Shores villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$2,120

The Lovely Guesthouse

Gulfport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$115

De Soleil South Beach Hotel on Ocean Drive

Miami Beach hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$343

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$589

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$820

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$623

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$413

Lakefront with Pool between Miami & Keys 4BD/2BTH

Cutler Bay house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Golf course on site or within 15 min walk, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$344

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